Originally published in 1845, The Narrative of the Life of Frederick Douglass, An American Slave gained instant recognition. Dubbed a “black Horatio Alger” and “black Franklin,” Frederick Douglass is known for sustaining the American tradition of the self-made man. This paper focuses on Douglass’s Narrative and its contemporary reception in regard to the myth of the self-made man. It examines Douglass’s strategies for identifying with his white audience which enable him to “textually pass” for white. While Douglass’s admitted assumption of “white” rhetorical strategies and cunning techniques for identifying with his white audience permit him to textually pass, passing for white is not the same as being white. Douglass is still limited by, as Homi Bhabha has coined, the appellation “not quite/not white.” While the “not quite” limits Douglass, the “not white” of Douglass’s body enables his readers to temporarily assume blackness. The blackface masks donned by white readers of Narrative, can assuage white guilt, but at the expense of masking the reality of white privilege. In the wake of the troubled discourses of multiculturalism and universal nationalism, readings of Douglass’s Narrative have the potential to promote the United States as “the land of opportunity” thereby veiling very real racial inequalities.